Carbon Dioxide → HCID 58551796, compound

HRID 2204223Notes

Reaction equation

HRID 2204223 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[CH3:13].[Li]CCCC.[C:19](=[O:21])=[O:20].Cl>C1COCC1>[CH:10]([O:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:19]([OH:21])=[O:20])=[C:3]([CH3:13])[CH:4]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 58551018HCID 58551018, compoundHCID 178418339Butyllithium

Product 1

HCID 58551796HCID 58551796, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-iodo-4-isopropoxy-2,5-dimethylbenzene (450 mg, 1.6 mmol) in THF (7.8 mL) was cooled to −78° C. before nBuLi (620 mL, 2.5 M, 1.6 mmol) was added dropwise. The mixture was allowed to warm to 0° C., then it was cooled to −78° C. before it was added dropwise to a flask containing crushed, dry CO2. The mixture was allowed to warm to room temperature and was stirred overnight. The mixture was poured over ice and was acidified with 1N HCl. The mixture was extracted with ethyl acetate (3×) and the combined organics were washed with brine, dried over sodium sulfate, and concentrated to give 4-isopropoxy-2,5-dimethylbenzoic acid (67 mg, 10%). ESI-MS m/z calc. 208.1, found 209.1 (M+1)+; Retention time: 1.55 minutes (3 min run).

Workup

  1. additionwas added dropwise
  2. temperatureit was cooled to −78° C. before it
  3. additionwas added dropwise to a flask
  4. additioncontaining
  5. customcrushed
  6. temperatureto warm to room temperature
  7. additionThe mixture was poured over ice
  8. extractionThe mixture was extracted with ethyl acetate (3×)
  9. washthe combined organics were washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2e0f0c8f5b4f4269aad78e4b15199836
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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